JP7059384B2 - ジブチルフルオレニル誘導体及びその光開始剤としての使用 - Google Patents
ジブチルフルオレニル誘導体及びその光開始剤としての使用 Download PDFInfo
- Publication number
- JP7059384B2 JP7059384B2 JP2020545844A JP2020545844A JP7059384B2 JP 7059384 B2 JP7059384 B2 JP 7059384B2 JP 2020545844 A JP2020545844 A JP 2020545844A JP 2020545844 A JP2020545844 A JP 2020545844A JP 7059384 B2 JP7059384 B2 JP 7059384B2
- Authority
- JP
- Japan
- Prior art keywords
- photocurable composition
- manufacture
- photoinitiator
- resists
- dibutylfluorenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000203 mixture Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000003973 paint Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000002966 varnish Substances 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 238000013500 data storage Methods 0.000 claims description 2
- 238000005530 etching Methods 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 238000004377 microelectronic Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000007650 screen-printing Methods 0.000 claims description 2
- 229910000679 solder Inorganic materials 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229920002120 photoresistant polymer Polymers 0.000 claims 1
- -1 9,9-dibutylfluorenyl Chemical group 0.000 description 31
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 238000004806 packaging method and process Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 239000012855 volatile organic compound Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GUFPTZQVPDTJQK-UHFFFAOYSA-N 1-(9,9-dibutylfluoren-2-yl)-2-methylpropan-1-one Chemical compound CC(C(=O)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(CCCC)CCCC)C GUFPTZQVPDTJQK-UHFFFAOYSA-N 0.000 description 3
- ARYVCEYCSTUDOH-UHFFFAOYSA-N 2-bromo-1-(9,9-dibutylfluoren-2-yl)-2-methylpropan-1-one Chemical compound BrC(C(=O)C1=CC=2C(C3=CC=CC=C3C=2C=C1)(CCCC)CCCC)(C)C ARYVCEYCSTUDOH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- DPPFREDTHDJUOI-UHFFFAOYSA-N 9,9-dibutylfluorene Chemical compound C1=CC=C2C(CCCC)(CCCC)C3=CC=CC=C3C2=C1 DPPFREDTHDJUOI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011087 paperboard Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 230000005469 synchrotron radiation Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OQPNDCHKFIHPBY-UHFFFAOYSA-N 1,2-dichloro-2-methylpropane Chemical compound CC(C)(Cl)CCl OQPNDCHKFIHPBY-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- ZYZWCJWINLGQRL-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-diol Chemical group C1=CC(O)(O)CC=C1C1=CC=CC=C1 ZYZWCJWINLGQRL-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711175135.1 | 2017-11-22 | ||
CN201711175135.1A CN108117616B (zh) | 2017-11-22 | 2017-11-22 | 二丁基芴基衍生物与其作为光引发剂的应用 |
PCT/CN2018/116999 WO2019101142A1 (fr) | 2017-11-22 | 2018-11-22 | Dérivés dibutylfluorène et application de ceux-ci en tant que photo-initiateur |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021504555A JP2021504555A (ja) | 2021-02-15 |
JP7059384B2 true JP7059384B2 (ja) | 2022-04-25 |
Family
ID=62227901
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020545844A Active JP7059384B2 (ja) | 2017-11-22 | 2018-11-22 | ジブチルフルオレニル誘導体及びその光開始剤としての使用 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11560362B2 (fr) |
EP (1) | EP3715381B1 (fr) |
JP (1) | JP7059384B2 (fr) |
CN (1) | CN108117616B (fr) |
WO (1) | WO2019101142A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108117616B (zh) * | 2017-11-22 | 2019-08-09 | 惠州市华泓新材料股份有限公司 | 二丁基芴基衍生物与其作为光引发剂的应用 |
JP6817503B1 (ja) * | 2019-05-29 | 2021-01-20 | 株式会社Dnpファインケミカル | カラーフィルタ用感光性着色樹脂組成物、硬化物、カラーフィルタ、及び表示装置 |
WO2021125132A1 (fr) * | 2019-12-20 | 2021-06-24 | 株式会社Adeka | Composé de carbamoyl-oxime, initiateur de polymérisation et composition polymérisable contenant ledit composé |
WO2022091711A1 (fr) * | 2020-10-27 | 2022-05-05 | 株式会社Dnpファインケミカル | Composition de résine colorée photosensible, produit durci, filtre coloré et dispositif d'affichage |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050049425A1 (en) | 2003-08-25 | 2005-03-03 | Pearson Jason Clay | Ethylenically-unsaturated red anthraquinone dyes |
JP2006512458A (ja) | 2002-12-27 | 2006-04-13 | サン・ケミカル・コーポレーション | 放射線硬化可能な水性組成物 |
US20150329662A1 (en) | 2012-12-23 | 2015-11-19 | Huizhou Huahong New Material Co., Ltd. | Alkylphenyl derivatives and application thereof as photoinitiator |
US20160332960A1 (en) | 2014-01-17 | 2016-11-17 | Samyang Corporation | Novel fluorenyl b-oxime ester compounds, photopolymerization initiator and photoresist composition containing the same |
JP2017149914A (ja) | 2016-02-26 | 2017-08-31 | 東京応化工業株式会社 | 硬化性樹脂組成物物 |
WO2018149370A1 (fr) | 2017-02-17 | 2018-08-23 | 常州强力先端电子材料有限公司 | Photoinitiateur de fluorenylaminocétone, son procédé de préparation et composition photodurcissable aux uv le contenant |
JP2018532851A (ja) | 2015-10-08 | 2018-11-08 | 常州強力電子新材料股▲ふん▼有限公司Cahngzhou Tronly New Electronic Materials Co.,Ltd. | フルオレン含有オキシムエステル類光開始剤、その合成、それを含有する感光性樹脂組成物及びその使用 |
JP2019507108A (ja) | 2015-12-15 | 2019-03-14 | 常州強力先端電子材料有限公司Changzhou Tronly Advanced Electronic Materials Co.,Ltd. | フルオレン類多官能光開始剤およびその製造ならびに使用、フルオレン類光開始剤含有感光性樹脂組成物およびその使用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6127130B2 (ja) | 2012-05-03 | 2017-05-10 | コリア リサーチ インスティテュート オブ ケミカル テクノロジー | 新規のオキシムエステルフルオレン化合物、およびこれを含む光重合開始剤、並びにフォトレジスト組成物 |
CN102766045B (zh) | 2012-07-31 | 2014-03-05 | 惠州市华泓新材料有限公司 | 二苯甲酮衍生物与其作为光引发剂的应用 |
CN104004395B (zh) | 2014-06-17 | 2016-08-17 | 广东美涂士建材股份有限公司 | 一种木皮用uv辊涂弹性底涂涂料及其制备方法与实施工艺 |
KR101907544B1 (ko) * | 2014-07-15 | 2018-10-15 | 도쿄 오카 고교 가부시키가이샤 | 감광성 조성물 및 화합물 |
CN107272336A (zh) | 2016-04-06 | 2017-10-20 | 常州强力先端电子材料有限公司 | 一种含芴类光引发剂的感光性树脂组合物及其应用 |
CN106883114B (zh) | 2015-12-15 | 2019-11-19 | 常州强力先端电子材料有限公司 | 一种芴类多官能度光引发剂及其制备和应用 |
KR102347918B1 (ko) | 2016-03-28 | 2022-01-05 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치 |
CN106010144B (zh) | 2016-06-20 | 2019-04-23 | 上海飞凯光电材料股份有限公司 | 一种uv-led固化用光纤涂覆树脂及其制备方法和应用 |
CN107793503A (zh) * | 2017-09-28 | 2018-03-13 | 大连天源基化学有限公司 | 一种紫外光引发剂及其合成方法 |
CN108117616B (zh) | 2017-11-22 | 2019-08-09 | 惠州市华泓新材料股份有限公司 | 二丁基芴基衍生物与其作为光引发剂的应用 |
-
2017
- 2017-11-22 CN CN201711175135.1A patent/CN108117616B/zh active Active
-
2018
- 2018-11-12 US US16/765,826 patent/US11560362B2/en active Active
- 2018-11-22 EP EP18881958.5A patent/EP3715381B1/fr active Active
- 2018-11-22 WO PCT/CN2018/116999 patent/WO2019101142A1/fr unknown
- 2018-11-22 JP JP2020545844A patent/JP7059384B2/ja active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006512458A (ja) | 2002-12-27 | 2006-04-13 | サン・ケミカル・コーポレーション | 放射線硬化可能な水性組成物 |
US20050049425A1 (en) | 2003-08-25 | 2005-03-03 | Pearson Jason Clay | Ethylenically-unsaturated red anthraquinone dyes |
US20150329662A1 (en) | 2012-12-23 | 2015-11-19 | Huizhou Huahong New Material Co., Ltd. | Alkylphenyl derivatives and application thereof as photoinitiator |
US20160332960A1 (en) | 2014-01-17 | 2016-11-17 | Samyang Corporation | Novel fluorenyl b-oxime ester compounds, photopolymerization initiator and photoresist composition containing the same |
JP2018532851A (ja) | 2015-10-08 | 2018-11-08 | 常州強力電子新材料股▲ふん▼有限公司Cahngzhou Tronly New Electronic Materials Co.,Ltd. | フルオレン含有オキシムエステル類光開始剤、その合成、それを含有する感光性樹脂組成物及びその使用 |
JP2019507108A (ja) | 2015-12-15 | 2019-03-14 | 常州強力先端電子材料有限公司Changzhou Tronly Advanced Electronic Materials Co.,Ltd. | フルオレン類多官能光開始剤およびその製造ならびに使用、フルオレン類光開始剤含有感光性樹脂組成物およびその使用 |
JP2017149914A (ja) | 2016-02-26 | 2017-08-31 | 東京応化工業株式会社 | 硬化性樹脂組成物物 |
WO2018149370A1 (fr) | 2017-02-17 | 2018-08-23 | 常州强力先端电子材料有限公司 | Photoinitiateur de fluorenylaminocétone, son procédé de préparation et composition photodurcissable aux uv le contenant |
Also Published As
Publication number | Publication date |
---|---|
WO2019101142A1 (fr) | 2019-05-31 |
CN108117616B (zh) | 2019-08-09 |
EP3715381B1 (fr) | 2024-06-12 |
EP3715381A4 (fr) | 2020-09-30 |
EP3715381A1 (fr) | 2020-09-30 |
CN108117616A (zh) | 2018-06-05 |
US20200385359A1 (en) | 2020-12-10 |
JP2021504555A (ja) | 2021-02-15 |
US11560362B2 (en) | 2023-01-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7059384B2 (ja) | ジブチルフルオレニル誘導体及びその光開始剤としての使用 | |
TWI406847B (zh) | 肟酯化合物及使用其之感光性樹脂組成物 | |
KR101700476B1 (ko) | 고감광도 카르바졸 옥심 에스테르계 광개시제, 그 제조방법 및 용도 | |
JP2514804B2 (ja) | 共重合性光開始剤 | |
KR101860511B1 (ko) | 비스옥심 에스테르 광개시제, 및 그의 제조방법과 용도 | |
KR102362859B1 (ko) | 중합성 기를 함유하는 플루오렌 옥심 에스테르 광 개시제, 및 이의 제조방법 및 용도 | |
US9353207B2 (en) | Alkylphenyl derivatives and application thereof as photoinitiator | |
KR101742473B1 (ko) | 카바졸 케톡심 에스테르 고-감광도 광개시제 | |
KR20190029707A (ko) | 플루오렌 광개시제, 그 제조 방법, 이를 갖는 광경화성 조성물, 및 광경화 분야에서 그 용도 | |
KR20160108532A (ko) | 니트로 함유 비스옥심 에스테르 광개시제, 및 그의 제조방법과 용도 | |
KR101883164B1 (ko) | 비대칭 디옥심에테르 화합물 및 그 제조 방법과 응용 | |
JP2012051927A (ja) | 粉末の形態での白色固体光開始剤およびその製造 | |
Chen et al. | Synthesis and preliminary photopolymerization envaluation of photopolymerizalbe type II photoinitiators BRA and TXRA | |
WO2016192610A1 (fr) | Composé d'ester acyloxime pour matériau durcissant aux uv, procédé de synthèse associé, et application associée | |
US4251341A (en) | Photoinitiators for UV-curable systems | |
CN102766045B (zh) | 二苯甲酮衍生物与其作为光引发剂的应用 | |
WO2016192611A1 (fr) | Composé ester d'oxime, son procédé de synthèse, et son application | |
Chen et al. | Synthesis and preliminary photopolymerization evaluation of novel photoinitiators containing phototrigger to overcome oxygen inhibition in the UV-curing system | |
CN112939779B (zh) | 适用于uv-led深层光聚合的对苯二甲酰甲酸酯型光引发剂及其制备方法 | |
JP7300108B2 (ja) | 硬化物の製造方法 | |
JPS5921638A (ja) | 不飽和化合物の光重合法 | |
JP5299838B2 (ja) | 10−ヒドロキシ−10−ナフチルメチルアントラセン−9(10h)−オン化合物及びその光ラジカル重合開始剤としての用途。 | |
CN116903580A (zh) | 适用于uv-led固化体系的单组份硫杂蒽酮类光引发剂及其制备与应用 | |
CN116947699A (zh) | 具有联苯结构的碘鎓盐化合物及其制备方法和应用 | |
JPS629110B2 (fr) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200621 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20210617 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210629 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210929 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220201 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220228 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20220405 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220413 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7059384 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |